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You do not need to install Windows in WINE because you can not. WINE creates its own directories to fool windows programs that it is running a version of windows.
For the first test to make sure WINE is working. Run notepad. The command should be "wine notepad". If you see notepad loaded then you got it running and it is properly configure. Next you can try to install iTunes. IMHO, WINE and codeweaver is not the best program to run iTunes. I suggest getting a MAC or try VMware for 30 days. VMware has stutter audio, but it is able to use USB devices like StereoLink without virtualizing it.
Mac on linux allows you to install OS X and you could install itunes on top of that.
Even I will not suggest this because I do not approve it. rcottere, I'm sorry that I have to be harsh. I suggest leaving MAC OS X to the Apple computers not to some emulation. All I can say it will be painfully slow and it will crash more than Windows.
You say you've had some progress with PearPC....I posted this thread on some other LQ (Fedora!) section:
"I have discovered that Pear PC is included in the list of programs that can be installed for FC3 from Synaptic...which I did out of curiosity....(Using virtual Mac on Linux!....wao!)....
Now it happens that it doesn't work at all...
I went to the Freshmeat page for PearPC and reading down it looks like there is no such program for FC3.
What's the deal here?"
Codeweavers atm is the only one that will run it afaik.
But if it's just to connect your ipod to your linux box, amarok and rhytmbox have experimental ipod support or look at http://gtkpod.sourceforge.net/
I haven't actually tested it, but I've researched it because my laptop is a Mac and my main box is linux/windows dual-boot. CodeWeavers Crossover Office is the only one that supports iTunes so far (unless there is something else that will "randomly" support it). You need version 4.0 for it to work. There are some bugs in it still and last I checked they were about to release 4.1 to fix the bugs. It might be out.
Yes it costs money to use. I think about $40 but to me it's worth it since it runs so many other aps. Using Visual Basic in Linux is an irony that cannot be ignored.
Have you tried to look at other music players? There's Juk on KDE which i'm starting to like. It may be similar to iTunes but i'm not sure because i don't have much experience with itunes. foobar2000 is my player of choice on windows. It works under wine, but the last time I tried it didn't refresh text correctly... it still played music though.
I think what some people want Itunes for is to buy music, not as a Jukebox or connect their Ipod. I have a music app I like, I have a non Apple MP3 player (Creative Labs Zen Jukebox, great linux support), but I'd like to browse the itunes store, but cannot without their software.